Aught Lang Syne: The Funniest Comedians of the Decade

Comedy is a broad subject. It’s not confined to any one medium, genre, style, or format. It’s hard to define and almost impossible to quantify. But here at NPI, we take comedy very seriously. The comedy of the Aughts in particular will always have an important role in shaping our senses of humor. So today we present a list, in no particular order, of people who helped to truly shape the comedy of the decade. This is not a list of people who were funny once or twice, but people with a body of work that is both rich and impressive. This means that a lot of people had to be cut. Great stand-up comics (Louis C.K., Aziz Ansari), some hilarious supporting comic actors (Paul Rudd, Jason Schwartzman), and even some groundbreaking comic teams (Flight of the Conchords, Stella), couldn’t make the list. And that’s because the following individuals/groups reached a level of success, both in terms of popularity and quality, that helped define the comedy of the decade.

The cast of Arrested Development

Arrested Development has the funniest ensemble cast in the history of comedic television, and it’s way ahead of whatever’s at #2. Tim has already extolled the virtues of Jason Bateman as Michael Bluth, but the fact is that the main character is about the sixth-funniest cast member on the show. Michael Cera gave a breakout performance for three years as George Michael, completely selling every awkward quirk of the character, including (and especially) his love for his cousin. David Cross played Tobias’ obliviousness and physical awkwardness to perfection, conveying every sexual inadequacy and illicit implication (“She said ‘single,’ right?”). Will Arnett made a magician named Gob come off as arrogant, creepy, and sympathetic. Portia Di Rossi played Lindsay’s self-righteousness and laziness as mutually coexisting. Jeffrey Tambor, as the family patriarch, managed to make the character so memorable that they had to keep him as a regular, even though he was supposed to remain a guest after the pilot. Tony Hale’s Buster, Jessica Walter’s Lucille, and Alia Shawkat’s Maeby, rounded out the cast, ensuring the show didn’t have a single weakness. Even guest stars, like Henry Winkler, Ed Begley, Jr., and John Michael Higgins, manage to turn their characters into memorable comic stars.

Most important, though, was the way the cast interacted. Plenty, if not all, great comedies have breakout characters and star performers, but few entire casts have had the chemistry that this cast had. Exchanges between Michael and his son, for example, are so great not just because of the dialogue and each character’s eccentricities, but because of the interplay between the two characters. Their ability to talk over each other, fill in each other’s awkward gaps, and respond nonverbally to the other’s lines are as funny as anything in the script.

Will Ferrell

In terms of pure popularity and commercial success, no comedian on this list has had a better decade than Will Ferrell. When the Aughts began, he was an underappreciated member of the Saturday Night Live cast, probably best known for playing Alex Trebek in Celebrity Jeopardy sketches, alongside Darrell Hammond’s Sean Connery. Now, he is one of the most highly paid, and perhaps the single most overpaid, stars in Hollywood.

And while his recent string of movies (Land of the Lost, Semi-Pro, Step Brothers) has not met with the kind of cultural response as some of his earlier work, it’s impossible to deny his imprint on the comedy of the decade.

Here’s a brief overview of comedy phenomena that Ferrell has had an integral hand in bringing to life this decade: his definitive impression of George W. Bush, More Cowbell, Jacobim Mugatu, Frank the Tank, Ron Burgundy, the Little Landlord, etc. This list still omits over half of his films, and plenty of his SNL sketches and viral hits. While some (myself included) think pretty much that whole list is comedy gold, it’s hard to really find anyone who doesn’t appreciate at least something there. Ferrell’s comedy sometimes gets criticized for being too broad or over-the-top, but the truth is that Ferrell’s ability to embody a comic persona so completely leads to just as many subtle, clever moments as big, outlandish ones. It’s the big, crazy ones that get remembered, of course, but even comedy elitists should be able to appreciate Ferrell’s unparalleled ability to make unfunny material sound hilarious.

Ricky Gervais & Stephen Merchant

You know who doesn’t get enough credit? Stephen Merchant. Ricky Gervais is a worldwide celebrity, but Merchant is a more or less unknown face. Without Merchant, though, Gervais’ impact on the comedy of the decade would not be as unmistakable as it is. His film career is rather forgettable on the whole; his stand-up, while very good, is not good enough to make this list on its own.

The real reason, of course, for Gervais and Merchant’s inclusion on the list is The Office. Possibly the most groundbreaking series of the decade, The Office was the first show to successfully use the documentary format in a series, the format since aped by the American version, Arrested Development, Parks & Recreation, etc. Even more important, though, is the way the show mined silence, awkwardness, and self-deception for rich comedy. The show, by veering more directly into the misanthropic than pretty much any other comedy, created one of the funniest series of the Aughts.

Extras, their follow-up, was an almost equally brilliant examination of celebrity and vanity. Extras was also noteworthy for finally giving Merchant the opportunity to share the screen with Gervais (with one small exception in The Office); given the opportunity, Merchant steals almost every scene.

Jon Stewart and The Daily Show writers

It’s weird to think that Jon Stewart was not the original host of The Daily Show, or that Stewart almost left to host a network show that ultimately went to Jimmy Kimmel, since Jon Stewart is, at this point, so linked to his show. It’s hard to imagine anyone else hosting it because Stewart’s mix of humility, indignity, intelligence, and relatability are so integral to its success. The Daily Show has survived the departure of so many star correspondents—Steve Carell, Stephen Colbert, Rob Corddry, Mo Rocca, Ed Helms, etc.—because Stewart is such a strong foundation for the show.

Stewart’s cultural relevance—his ability to take down Crossover, to tear apart Jim Cramer—often cloud how funny the show has been throughout the decade. While it has a tendency to rest on its laurels—and Stewart’s ability to sell a mediocre joke—the show still knows how to bring the smartest satire to news and cable programming. Every election season, the show seems to hit a new stride. In fact, the comedy generated out of politics is almost taken for granted as an intrinsic part of politics now; it is hard to imagine the current political landscape existing without Jon Stewart and The Daily Show.

Stephen Colbert

Unlike The Daily Show, in which Jon Stewart serves as an anchor for a large cast of correspondents lampooning the entire spectrum of political coverage, The Colbert Report is really all about Stephen Colbert. Colbert’s character of Stephen Colbert is what sells the comedy on his show. What Colbert has done, then, is probably more impressive than what Stewart has done, particularly when you consider that The Colbert Report is, at this point, more consistently funny and relevant than The Daily Show. Colbert has made such an art of getting politicians and public figures to embarrass themselves that he’s had to more or less abandon “Better Know a District,” one of his funniest features, due to the refusal of Congressmen to meet with him.

Stephen Colbert is best known for his own show—and for his use of the character in other venues, like Ben & Jerry’s flavors, and the White House Correspondence dinner—but, of course, he has had a strong career outside of it. He was the best correspondent on The Daily Show during his time on that show, bringing such highlights as “This Week in God” and “Even Stevphen.” And I would be remiss if I omitted the cult hit Strangers with Candy, which he co-wrote, co-created, and co-starred in. The majority of that series aired in 2000, to little audience reaction but high quality, and the film adaptation came out in 2006. Colbert’s comic talents have a wide range, but the character he has fashioned on his own show is clearly him at his most memorable.

Dave Chappelle

It’s probably easily forgotten at this point, but when Chappelle’s Show premiered in 2003, it generated buzz in a way that no show has really done since. Usually, comedians who get a lot of attention for “controversial” treatment of racial subjects are using taboo material as a crutch for bad jokes (read: Carlos Mencia). Chappelle, however, is to racial humor what Woody Allen was to Jewish humor, or The Daily Show is to political humor: He did it in a way that was completely clever, original, and, most of all, funny. Skits like “The Racial Draft” and “The Black White Supremacist” went beyond traditional “black people are different than white people” tropes, and managed to find new ways to mock racial sensitivity. The show also had plenty of forgotten gems that hardly touched on race, such as “Better in Slow Motion,” “The Three Daves,” and “Great Moments in Hookup History.” 

Of course, all anyone seems to remember from Chappelle’s Show is “I’m Rick James, bitch!” which was basically why he walked away from the show after two seasons. Truthfully those 25 episodes would have probably been enough to get him on the list, given their cultural impact, but Chappelle was also one of the best stand-up comics of the decade. Killing Them Softly and For What It’s Worth are two of the best specials of the decade, including his bit on Sesame Street and his trip to the ghetto.

Mitch Hedberg

It may be mildly surprising that Mitch Hedberg is on this list, being that he passed away halfway through the decade. For anyone who knows his material, though, Hedberg’s impact on stand-up comedy, even given his unfortunately early death, is unmistakable.* Hedberg was so personable and distinctive in his voice and mannerisms that he managed to create a memorable stand-up persona, despite the fact that his material is basically a series of unconnected one-liners. His deftness with punchlines, though, made his jokes some of the most memorable ones of the Aughts.

*When I first heard about Hedberg’s death, on March 30, 2005, I convinced myself it was an elaborate and early April Fools’ joke for almost a week.

Strategic Grill Locations, Hedberg’s first CD, technically came out in 1999 but didn’t start circulating widely until 2000 (it was originally self-published). It very quickly, however, established Hedberg’s voice and wit, including lines like, “A severed foot is the ultimate stocking-stuffer,” and “I opened up a yogurt and underneath the lid it said, ‘Please try again,’ because they were having a contest I was unaware of. But I thought I might have opened the yogurt wrong. Or maybe Yoplait was trying to inspire me.” His follow-up, Mitch All-Together, was released in 2003, and continued Hedberg’s warped brand of observational comedy. Losing arguably the best stand-up comic at the age of 37 was probably the worst tragedy to afflict comedy in the Aughts.

Zach Galifianakis 

Until 2009’s The Hangover, Zach Galifianakis wasn’t really a household name, or even a name you could really be sure other comedy fans had heard of. Now, though, even if people don’t know his name, they know of “the guy from The Hangover.” But this doesn’t mean that Galifianakis wasn’t producing great comedy throughout the decade; it was merely that none of his projects ended up catching on, usually because they weren’t the right fit for his talents. His Comedy Central Presents was hilarious and original, but very offbeat, featuring a 12-piece a capella group at the end. His VH1 talk show had some great moments, but forced him to be too mainstream. His appearances as Seth Galiafinakis never really had a big platform. He excelled on Dog Bites Man, but the show was cancelled after one season on Comedy Central.

In every one of these venues, though, Galifianakis brought his brilliantly absurd style of comedy to the project, making it both original and funny. The things that bear his pure creative stamp, including his stand-up comedy and his talk show, Between Two Ferns, were consistently unpredictable and hilarious.

Larry David

Obviously, we here at NPI are big fans of Curb Your Enthusiasm, so it shouldn’t be a surprise that Larry David makes the list of funniest people of the decade. As the star and creative force behind one of the best comic series of the decade, David’s stamp on the comedy of the Aughts is unmistakable. Curb Your Enthusiasm, in fact, may be the best series to run the full length of the decade (although that’s a little unfair, since HBO allows David to take large gaps between the seasons). The improvisational style leads to great moments from Jeff Garlin, Cheryl Hines, Bob Einstein, J.B. Smoove, Susie Essman, and the rest of the cast, but it’s Larry that holds the show together. As the social misanthrope who isn’t afraid to challenge any cherished societal convention, Larry David has produced a character who is relatable and likable, despite the fact that so much of what he does is so detestable. 

Curb Your Enthusiasm has both extended the Seinfeld-style of humor and left an even stronger “Larry David” signature on the world of comedy. When David starred in Woody Allen’s Whatever Works this summer, it was an example of two stars of Jewish comedy coming together. But what it really demonstrated was how much more natural and innovative David’s own style seems, at this point, than someone even as groundbreaking as Woody Allen.


Trey Parker & Matt Stone

South Park really peaked in popularity in the late 1990s, shortly after the show debuted. The show was a phenomenon right from the start, thanks to the crude humor of Cartman and the rest. Even the movie South Park: Bigger, Longer & Uncut came out in 1999. It was during this decade, however, that the show hit its creative stride. Since the show is so well-known for its fart jokes and scatological material—which it has never abandoned—the cleverness of its wit and satire is often overlooked.

The ability of Trey Parker and Matt Stone to satirize and mock things like the reaction to Hurricane Katrina, World of Warcraft, and elections shows that they are really the smartest and most original social commentators on television right now. 

Parker and Stone are also admirable for their willingness to go after things that aren’t generally criticized, like anti-smoking backlash and the comedy of Family Guy. Their show, in addition to being one of the most consistently funny shows on television, is one of the few comedies that actually makes a strong and persuasive argument about something, on occasion. This, of course, is not a requirement of comedy, but it does make satire funnier when it comes from a real place.

Judd Apatow

Judd Apatow has had a hand in some of the funniest movies of the decade. His work on television from the early part of the Aughts—Freaks and Geeks and Undeclared—is often heralded as a more mature kind of comedy, but Apatow’s real strength would be in movies. He directed and co-wrote The 40-Year-Old Virgin; he wrote and directed Knocked Up. He was also the producer on Anchorman, Talladega Nights, Superbad, Walk Hard, Forgetting Sarah Marshall, Pineapple Express, as well as a few others.

His effect on the world of comedy, though, extends far beyond his own films. He has helped make stars out of Seth Rogen, Jason Segel, and Paul Rudd. He has helped revive the career of Adam Sandler (for better or for worse). He has developed a certain style and tone of male dialogue that will be ripped off for years, and his role in shaping the modern romantic comedy genre is unmistakable.

Conan O’Brien

The recent press around Conan O’Brien’s move to The Tonight Show has not been good: His ratings have fallen and many people are already predicting his demise as host. In some ways, this just confirms the feelings of Conan’s biggest fans: Most people don’t get him. Conan has never shied away from the fact that his style of humor is somewhat more outlandish and goofy than that of other late-night hosts. This means that the audience that tuned in to hear Jay Leno make generic jokes about current events might not find the appeal of Conan’s attempts to alienate every country.

But for many, particularly in younger demographics, Conan continues to be the funniest and most exciting late-night host. He single-handedly resuscitated Chuck Norris’ career, he made the most of his trips to Chicago and Finland, and, of course, he explored the intricacies of old-timey baseball. His willingness to do these absurd features makes him totally unique among late-night hosts.

5 responses to this post.

  1. […] Aught Lang Syne « Aught Lang Syne: The Funniest Comedians of the Decade […]


  2. […] Career: I’m as a big a Michael Cera fan as you will find: He was possibly the funniest part of the funniest show of the Aughts, and he was certainly the funniest part of the funniest film of the Aughts. Even I have to admit, […]


  3. […] case you haven’t heard by now, NBC has decided to screw one of the best comedians of the last decade. Conan O’Brien, less than a year into his run as the host of The Tonight Show, is being bumped […]


  4. […] you haven’t been paying attention to this blog for the last 11 months, then you may not have realized that I was looking forward to last night’s premiere of Conan on […]


  5. […] Mitch Hedberg […]


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